Ligand-centred Chemistry of Molybdenum Organoimides. Formation of C-C Bonds via Generation of Nitrogen Ylides, Stereospecific Conversion of an Allylimide into Alkylvinylimides, Liberation of Cyanoformate or Amino Acid Esters

DOI: 10.1039/DT9950001973

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 1973 - 1984 (1995)

Update date:2022-08-03

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Authors:

Fairhurst, Shirley A.

Hughes, David L.

Ibrahim, Saad K.

Abasq, Marie-Laurence

Talarmin, Jean

et al. et al.

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Article abstract of DOI:10.1039/DT9950001973

The range of imides trans-(1+) made from the nitride trans- (dppe = Ph2PCH2CH2PPh2, R1 = H or organic group, R2 = organic group) has been extended; deprotonation of the imide group at the α-carbon gives reactive alkenylamides which have nitrogen ylide character and these are attacked by electrophiles.Stepwise C1 homologation of a methylimide to ethyl- and isopropyl-imides can be achieved by successive deprotonation and methylation steps.The crystal structure of the alkenylamide trans- has been determined, as has that of the imide produced directly from it by C-methylation, trans-2>(1+).Deprotonation at the α-carbon of an allylimide complex gives a species which is regioselectively and stereospecifically attacked by electrophiles at the γ-carbon; when the electrophile is the proton the overall reaction corresponds to a 1,3-prototropic rearrangement of the allylimide to the E-methylvinylimide.Electroreduction of imides in the presence of a source of protons releases the free amine; in this way esters of the amino acids glycine and DL-alanine have been synthesised.Two protons can be removed by base from imides with electron-withdrawing ester substituents and free cyanoformate esters are released from the metal centre by substitution with dinitrogen or CO.

Full text of DOI:10.1039/DT9950001973

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